Use of a composition and a method for the promotion of plant production and/or for the elimination of the unfavorable influences in plant cultivation

Abstract

Compositions containing hydroximic acid derivatives of the formula where R 1 , R 2 , R 3 , R, X, Y, A, and B are as defined in the specification, are useful for the promotion of plant production and/or for the elimination of unfavourable environmental influences in plant cultivation.

We claim:  
     
       1. A composition for the promotion of plant production and/or for the elimination of unfavorable environmental influences in plant cultivation comprising: 
       a hydroximic acid derivative of the formula                    
        where  
       R 1  is a hydrogen atom or a C 1-5  alkyl group,  
       R 2  is a hydrogen atom, a C 1-5  alkyl group, a C 3-8  cycloalkyl group, or a phenyl group optionally substituted with a hydroxy or a phenyl group, or  
       R 1  and R 2  together with the nitrogen atom to which they are attached form a 5- to 8-membered ring optionally containing one or more further nitrogen, oxygen, or sulfur atoms, the ring being optionally condensed with another alicyclic or heterocyclic ring, and the nitrogen and/or sulfur atoms being optionally present in the form of an oxide or dioxide,  
       R 3  is a hydrogen atom, a phenyl group, a naphthyl group, or a pyridyl group, each of these groups being optionally substituted with one or more halo atoms or C 1-4  alkoxy groups,  
       Y is a hydrogen atom, a hydroxy group, a C 1-24  alkoxy group optionally substituted with an amino group, a C 2-24  polyalkenyloxy group containing 1 to 6 double bonds, a C 1-25  alkanoyl group, a C 3-9  alkenoyl group, or a group of the formula R 7 COO— where R 7  is a C 2-30  polyalkenyl group containing 1 to 6 double bonds,  
       X is a halo atom, an amino group, or a C 1-4  alkoxy group, except that X is not an amino group if Y is a hydroxy group, or  
       X and B together are an oxygen atom, or X and Y together with the carbon atoms to which they are attached and the —NR—O—CH 2 — group between these carbon atoms form a ring of the formula                    
       where Z is an oxygen atom or a nitrogen atom, 
       R is a hydrogen atom, or  
       R and B together are a chemical bond,  
       A is a C 1-4  alkylene group, a chemical bond, or a group of the formula                    
        where  
       R 4  is a hydrogen atom, a C 1-5  alkyl group, a C 3-8  cycloalkyl group, or a phenyl group optionally substituted by a halo atom, a C 1-4  alkoxy group, or a C 1-5  alkyl group,  
       R 5  is a hydrogen atom, a C 1-4  alkyl group, or a phenyl group,  
       m is 0, 1, or 2, and  
       n is 0, 1, or 2,  
       or a physiologically acceptable acid addition salt thereof, as the active ingredient, 
       in admixture with at least one conventional solid or liquid carrier of compositions used in plant protection. 
     
     
       2. A composition of claim  1  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1  and R 2  together with the nitrogen atom to which they are attached form a 5- to 8-membered ring optionally containing one or more further nitrogen, oxygen, or sulfur atoms, the ring being condensed with a benzene, naphthalene, quinoline, isoquinoline, pyridine, or pyrazoline ring, the nitrogen and/or sulfur atoms being optionally present in the form of an oxide or dioxide,  
       R 3 , R, X, Y, A, and B are as defined in claim  1 ,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       3. A composition of claim  1  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1 , R 2 , R 3 , R 4 , R 5 , m, and n are as defined in claim  1 ,  
       X is a halo atom or an amino group, and  
       Y is a hydroxy group,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       4. A composition of claim  1  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1 , R 2 , R 3 , and A are as defined in claim  1 ,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       5. A composition of claim  1  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1 , R 2 , R 3 , and A are as defined in claim  1 , and  
       Z is an oxygen atom or a nitrogen atom,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       6. A composition of claim  1  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1 , R 2 , R 3 , and A are as defined in claim  1 , and  
       R 6  is a C 1-4  alkyl group,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       7. A composition of claim  3  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 3 , X, and Y are as defined in claim  3 ,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       8. The composition of claim  7  in which the hydroximic acid derivative is N-[2-hydroxy-3-(1-piperidinyl)propoxy]-3-pyridine-carboximidoyl chloride or a physiologically acceptable acid addition salt thereof. 
     
     
       9. A composition for the treatment of a plant to be cultivated or a seed, seedling, leaf, or root thereof for the promotion of plant production and/or for the elimination of unfavorable environmental influences in plant cultivation comprising: 
       an effective non-toxic amount from 0.0001% to 1.0% by mass of the composition of a hydroximic acid derivative of the formula                    
       where 
       R 1  is a hydrogen atom or a C 1-5  alkyl group,  
       R 2  is a hydrogen atom, a C 1-5  alkyl group, a C 3-8  cycloalkyl group, or a phenyl group optionally substituted with a hydroxy or a phenyl group, or  
       R 1  and R 2  together with the nitrogen atom to which they are attached form a 5- to 8-membered ring optionally containing one or more further nitrogen, oxygen, or sulfur atoms, the ring being optionally condensed with another alicyclic or heterocyclic ring, and the nitrogen and/or sulfur atoms being optionally present in the form of an oxide or dioxide,  
       R 3  is a hydrogen atom, a phenyl group, a naphthyl group, or a pyridyl group, each of these groups being optionally substituted with one or more halo atoms or C 1-4  alkoxy groups,  
       Y is a hydrogen atom, a hydroxy group, a C 1-24  alkoxy group optionally substituted with an amino group, a C 2-24  polyalkenyloxy group containing 1 to 6 double bonds, a C 1-25  alkanoyl group, a C 3-9  alkenoyl group, or a group of the formula R 7 COO— where R 7  is a C 2-30  polyalkenyl group containing 1 to 6 double bonds,  
       X is a halo atom, an amino group, or a C 1-4  alkoxy group, except that X is not an amino group when Y is a hydroxy group, or  
       X and B together are an oxygen atom, or  
       X and Y together with the carbon atoms to which they are attached and the —NR—O—CH 2 — group between these carbon atoms form a ring of the formula                    
       where Z is an oxygen atom or a nitrogen atom, 
       R is a hydrogen atom, or  
       R and B together are a chemical bond,  
       A is a C 1-4  alkylene group, a chemical bond, or a group of the formula                    
        where  
       R 4  is a hydrogen atom, a C 1-5  alkyl group, a C 3-8  cycloalkyl group, or a phenyl group optionally substituted by a halo atom, a C 1-4  alkoxy group, or a C 1-5  alkyl group,  
       R 5  is a hydrogen atom, a C 1-4  alkyl group, or a phenyl group,  
       m is 0, 1, or 2, and  
       n is 0, 1, or 2,  
       or a physiologically acceptable acid addition salt thereof, as the active ingredient, 
       in admixture with at least one conventional solid or liquid carrier of compositions used in plant protection. 
     
     
       10. A composition of claim  9  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1  and R 2  together with the nitrogen atom to which they are attached form a 5- to 8-membered ring optionally containing one or more further nitrogen, oxygen, or sulfur atoms, the ring being condensed with a benzene, naphthalene, quinoline, isoquinoline, pyridine, or pyrazoline ring, the nitrogen and/or sulfur atoms being optionally present in the form of an oxide or dioxide,  
       R 3 , R, X, Y, A, and B are as defined in claim  9 ,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       11. A composition of claim  9  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1 , R 2 , R 3 , R 4 , R 5 , m, and n are as defined in claim  9 ,  
       X is a halogen atom or an amino group, and  
       Y is a hydroxy group,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       12. A composition of claim  9  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1 , R 2 , R 3 , and A are as defined in claim  9 ,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       13. A composition of claim  9  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1 , R 2 , R 3 , and A are as defined in claim  9 , and  
       Z is an oxygen atom or a nitrogen atom,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       14. A composition of claim  9  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 1 , R 2 , R 3 , and A are as defined in claim  9 , and  
       R 6  is a C 1-4  alkyl group,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       15. A composition of claim  11  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 3 , X, and Y are as defined in claim  11 ,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       16. The composition of claim  15  in which the hydroximic acid derivative is N-[2-hydroxy-3-(1-piperidinyl)propoxy]-3-pyridine-carboximidoyl chloride or a physiologically acceptable acid addition salt thereof. 
     
     
       17. A method for the promotion of plant production and/or for the elimination of unfavorable environmental influences in plant cultivation comprising treatment of a plant to be cultivated or a seed, seedling, leaf, or root thereof with an effective non-toxic amount of a hydroximic acid derivative of the formula                    
       where 
       R 1  is a hydrogen atom or a C 1-5  alkyl group,  
       R 2  is a hydrogen atom, a C 1-5  alkyl group, a C 3-8  cycloalkyl group, or a phenyl group optionally substituted with a hydroxy or a phenyl group, or  
       R 1  and R 2  together with the nitrogen atom to which they are attached form a 5- to 8-membered ring optionally containing one or more further nitrogen, oxygen, or sulfur atoms, the ring being optionally condensed with another alicyclic or heterocyclic ring, and the nitrogen and/or sulfur atoms being optionally present in the form of an oxide or dioxide,  
       R 3  is a hydrogen atom, a phenyl group, a naphthyl group, or a pyridyl group, each of these groups being optionally substituted with one or more halo atoms or C 1-4  alkoxy groups,  
       Y is a hydrogen atom, a hydroxy group, a C 1-24  alkoxy group optionally substituted with an amino group, a C 2-24  polyalkenyloxy group containing 1 to 6 double bonds, a C 1-25  alkanoyl group, a C 3-9  alkenoyl group, or a group of the formula R 7 COO— where R 7  is a C 2-30  polyalkenyl group containing 1 to 6 double bonds,  
       X is a halo atom, an amino group, or a C 1-4  alkoxy group, except that X is not an amino group when Y is a hydroxy group, or  
       X and B together are an oxygen atom, or  
       X and Y together with the carbon atoms to which they are attached and the —NR—O—CH 2 — group between these carbon atoms form a ring of the formula                    
       where Z is an oxygen atom or a nitrogen atom, 
       R is a hydrogen atom, or  
       R and B together are a chemical bond,  
       A is a C 1-4  alkylene group, a chemical bond, or a group of the formula                    
        where  
       R 4  is a hydrogen atom, a C 1-5  alkyl group, a C 3-8  cycloalkyl group, or a phenyl group optionally substituted by a halo atom, a C 1-4  alkoxy group, or a C 1-5  alkyl group,  
       R 5  is a hydrogen atom, a C 1-4  alkyl group, or a phenyl group,  
       m is 0, 1, or 2, and  
       n is 0, 1, or 2,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       18. The method of claim  17  in which the treatment comprises administration of a composition comprising 0.0001% to 1.0% by mass of the composition of the hydroximic acid derivative or a physiologically acceptable acid addition salt thereof. 
     
     
       19. The method of claim  17  in which the hydroximic acid derivative is a compound of the formula                    
       where 
       R 3  is as defined in claim  17 ,  
       X is a halo atom or an amino group, and  
       Y is a hydroxy group,  
       or a physiologically acceptable acid addition salt thereof. 
     
     
       20. The method of claim  19  in which the hydroximic acid derivative is N-[2-hydroxy-3-(1-piperidinyl)propoxy]-3-pyridine-carboximidoyl chloride or a physiologically acceptable acid addition salt thereof.